In my experience, having an entity is more useful from a liability perspective if, among other reasons, you're a passive owner, if you have multiple owners (particularly if some of them are passive and you are the controlling owner), if you have more complicated operations or if you have employees.

As far as I know the "substitute trustee" where you have "trustee auctions" is just a substitute representing the bank.....they don't own/control the actual property until after/if they get it back at the auction.  

Part of being a good employee is knowing when to be sensitive to issues you have no control of or responsibility for.. any questions just say I'd think you could talk with the owner or management. 

In this situation, you're still in control of the title and collecting rent. 

I am 60 years old now and the bulk of my experience was in the construction business doing all kinds of positions from actually doing building, accounting, estimating, and funding control, etc..

You have only so much control over the purchase price - you need a seller willing to agree to your math.

Piggybacking on question 2, how do most people calculate appropriate rent raises on a non-rent controlled property?

On the left end of the lever is the cash you put into the deal, on the right end is the property you control. 

Along these same lines, does anyone know if passing on the utility cost to the tenants would count as a 'rent increase' under the new rent control law?

I would still get the previous owner to deliver one unit vacant if you can and check if you're in a rent control area.Also FHA loans have pretty strict rules regarding total rent needed to qualify and price limits.